The location, the style of the home, and the long-term, cash flow opportunity.

I would look at the surrounding comps and see how they are decorated.

We rebuilt the front and back deck, replaced the hot tub cover/added a flipper, added more patio furniture, replaced the ugly flooring (cheap wood laminate/linoleum in bathrooms) downstairs, redecorated the entire inside, changed out dated light fixtures/fans, added small furniture pieces and decor to make it feel welcoming, added arcade games, purchased books/games/art, and adding a cabin name sign at street/on house.  

So you can certainly have a DSCR/commercial style lender just base the loan off of the rental income to refinance it.  

I will be a remote STR host and I will need somebody to keep the yard in good shape and shovel the (occasional) snow.My HUNCH is there must be some kind of Uber/Lyft/AIRBNB-style crowdsourcing platform for these kinds of services.

Can be a lux style or plex.

Only thing I wish I would have done is use equity to expand... with the caveat of ensuring i'm not over leveraged in case of a 2008/2009 style crash.  

If it were me, I would get them leased up asap and then sell them, perform a 1031 exchange to defer taxes on any gains and buy newer townhouse style apartments that cash flow.

At this point I’m looking for ranch style homes with good roofs (none flat), furnace/AC mid life or better, brick exterior is a bonus, double pane windows, younger than 1950’s.

In Orlando (at least), the typical thinking is to buy as big as you can afford, there are fewer of the larger homes and you also have much more flexibility to decorate and theme them with more square feet and #bedrooms.